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Synlett 2005(8): 1223-1234
DOI: 10.1055/s-2005-865237
DOI: 10.1055/s-2005-865237
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Towards the Synthesis of Ladder Oligo(p-aniline)s
Further Information
Received
11 December 2004
Publication Date:
21 April 2005 (online)
Publication History
Publication Date:
21 April 2005 (online)
Abstract
Using Cadogan or copper-catalyzed Ullmann reaction, new shape-persistent ladder oligo(p-aniline)s were synthesized from 2,7-carbazole derivatives. Physical characterization of these electroactive and photoactive organic materials is also presented.
1 Introduction
2 Synthesis of Ladder Oligo(p-aniline)s via the Cadogan Ring-Closure Reaction
2.1 Indolocarbazole Derivatives
2.2 Diindolocarbazole Derivatives
2.3 An Approach to the Synthesis of a Tetramer
3 Synthesis of Ladder Oligo(p-aniline)s via the Copper-Catalyzed Ullmann Ring-Closure Reaction
3.1 Diindolocarbazole Derivatives
3.2 Tetramer Derivatives
4 Characterization of the Ladder Oligo(p-aniline)s
5 Conclusion
Key words
carbazoles - oligoanilines - Cadogan reaction - Ullmann reaction - ladder oligomers
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References
1H NMR (400 MHz, THF-d 8): δ = 9.98 (s, 2 H, NH), 8.29 (d, 2 H, J = 2.0 Hz), 8.20 (s, 2 H), 8.15 (s, 2 H), 8.05 (s, 2 H), 7.46 (dd, 2 H, J = 8.5, 2.0 Hz), 7.40 (d, 2 H, J = 8.6 Hz), 4.50 (t, 4 H, J = 7.2 Hz), 1.97 (m, 4 H), 1.40 (3 m, 20 H), 0.86 (t, 6 H, J = 6.8 Hz). HRMS: m/z calcd for C46H48N4Br2: 814.2245; found: 814.2227.